tert-Butyl peroxybenzoate, TBPB
Recent Literature
The reaction of tert-butyl peroxybenzoate (TBPB) and ammonia/amines
provides the corresponding primary, secondary, and tertiary amides under
catalyst- and solvent-free conditions in excellent yields. TBPB is an efficient
and highly chemoselective benzoylating reagent for aliphatic amines in the
presence of aromatic amines and hydroxyl groups.
D. K. T. Yadav, B. M. Bhanage,
Synlett, 2015, 26, 1862-1866.
A mild protocol for the α-C-H cyanation of tertiary aliphatic, benzylic,
and aniline-type substrates and complex substrates tolerates a broad range of
fuctional groups, including various heterocycles and ketones, amides, olefins,
and alkynes. The presented catalyst system especially tolerates functional
groups that typically react with free radicals, suggesting an alternative
reaction pathway.
O. Yilmaz, C. Dengiz, M. H. Emmert, J. Org. Chem., 2021, 86,
2489-2498.
A radical-promoted decarboxylation enables a transition-metal-free
phosphorylation of cinnamic acids with P(O)H compounds under mild conditions.
This method provides simple, efficient, and versatile access to a broad range of
valuable (E)-alkenylphosphine oxides in good yields.
L. Liu, D. Zhou, J. Dong, Y. Zhou, S.-F. Yin, L.-B. Han, J. Org. Chem., 2018, 83,
4190-4196.
A convenient and general atom transfer radical addition (ATRA) of simple
nitriles, ketones, and esters to alkynes provides a wide range of
β,γ-unsaturated nitriles, ketones, and esters.
Y. Xiao, Z.-Q. Liu,
Org. Lett., 2019, 21, 8810-8813.
A convenient and general atom transfer radical addition (ATRA) of simple
nitriles, ketones, and esters to alkynes provides a wide range of
β,γ-unsaturated nitriles, ketones, and esters.
Y. Xiao, Z.-Q. Liu,
Org. Lett., 2019, 21, 8810-8813.
Visible-light irradiation mediates the synthesis of alkynylsilanes in very good
yields from alkynes and silanes in the presence of CuCl as precatalyst. A large
scale flow reaction and late-stage functionalization of natural products show
the potential of the transformation.
Q.-C. Gan, Z.-Q. Song, C.-H. Tung, L.-Z. Wu, Org. Lett.,
2022, 24, 5192-5196.
An efficient I2/TBPB mediated oxidative formal [4 + 1]
cycloaddition of N-tosylhydrazones with anilines represents a simple,
general, and efficient approach for the construction of 1,2,3-triazoles under
metal-free and azide-free conditions.
Z.-J. Cai, X.-M. Lu, Y. Zi, C. Yang, L.-J. Shen, J. Li, S.-Y. Wang, S.-J. Ji, Org. Lett.,
2014,
16, 5108-5111.
An oxidative cascade cyclization strategy enables an unprecedented
construction of thiazole-2-thiones from enaminones via a cascade of C(sp2)-H/C(sp2)-H
bond sulfurations and C(sp3)-H bond thiocarbonylation. This
transformation allows for the efficient synthesis of thiazole-2-thiones with
broad tolerance in moderate to excellent yields from simple enaminones with
elemental sulfur.
B. Zhan, D. Liu, Y. Sun, Y. Zhang, J. Feng, F. Yu, Org. Lett., 2021, 23,
3076-3082.
A nickel-catalyzed reaction of acrylamides or enamides with diazoacetates
provides indolin-2-ones or 1,4-dicarbonyl compounds in the presence of a peroxide
and ethanol as hydrogen source and solvent.
J. Zhao, P. Li, Y. Xu, Y. Shi, F. Li,
Org. Lett., 2019, 21, 9386-9390.
